Abacavir (CED0002764)

Record Information

Version

1.0

Creation Date

2016-05-22 05:44:50 UTC

Update Date

2026-08-19 06:29:59 UTC

Accession Number

CHEM018996

Identification

Common Name

Abacavir

Class

Small Molecule

Description

Abacavir is an organic compound with the chemical formula C14H18N6O and an average molecular weight of 286.34 g/mol. Abacavir belongs to the cyclopentyl nucleosides, a subclass of nucleoside and nucleotide analogues within the organic compounds. This compound is recorded as being found in or released from four sources: electrical and electronic equipment, specifically video games and television systems; healthcare, pharmaceuticals, and veterinary products, specifically antivirals; and household cleaning and consumer products, specifically non electric simulated smoking devices. The recorded route of exposure for this substance is oral. In terms of biological activity, abacavir acts on two recorded protein targets, serving as an inhibitor of the Gag-Pol polyprotein (gag-pol) and Reverse transcriptase/RNaseH (pol).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈N₆O

Average Molecular Mass

286.339 g/mol

Monoisotopic Mass

286.154 g/mol

CAS Registry Number

136470-78-5

IUPAC Name

[(1S,4S)-4-[6-(cyclopropylamino)-2-imino-2,9-dihydro-1H-purin-9-yl]cyclopent-2-en-1-yl]methanol

Traditional Name

[(1S,4S)-4-[6-(cyclopropylamino)-2-imino-1H-purin-9-yl]cyclopent-2-en-1-yl]methanol

SMILES

[H][C@]1(CO)C[C@@]([H])(C=C1)N1C=NC2=C(NC3CC3)NC(=N)N=C12

InChI Identifier

InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10-/m1/s1

InChI Key

MCGSCOLBFJQGHM-PSASIEDQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

Cyclopentyl nucleosides

Direct Parent

1,3-substituted cyclopentyl purine nucleosides

Alternative Parents

Substituents

1,3-substituted cyclopentyl purine nucleoside
6-alkylaminopurine
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
N-substituted imidazole
Pyrimidine
Imidolactam
Heteroaromatic compound
Azole
Imidazole
Secondary amine
Organoheterocyclic compound
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Primary amine
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	-0.17	ALOGPS
logP	-0.34	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	96.1 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.23 m³·mol⁻¹	ChemAxon
Polarizability	30.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-0090000000-0946b359f044edc1eaa7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-2190000000-64675b2273332e37f39a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9410000000-d05153b2e67c168956b2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-2944c593361dbd76b614	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-2390000000-06a2fd880fff3ed2e268	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9630000000-7c461fd855fa0cc2d7b1	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1298.0	Log mg/kg	[730:2300]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
351	Antivirals	Healthcare, pharmaceuticals & veterinary products	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Abacavir Action Pathway

Abacavir Action Pathway (New)

Abacavir Drug Metabolism

Abacavir Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	157.956
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	181.311
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	139.194
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	63.9142
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	123.08
Click to view 3D structure	Adenosine receptor A1	P28190	Bos taurus	Predicted (SEA)	56.8299
Click to view 3D structure	Adenosine receptor A2b	P29275	Humans	Predicted (SEA)	130.008
Click to view 3D structure	A1 adenosine receptor	Q4VQ11	Sus scrofa	Predicted (SEA)	21.7199
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	119.187
Click to view 3D structure	Adenosine receptor A3	Q61618	Mus musculus	Predicted (SEA)	41.3379
Click to view 3D structure	Adenosine receptor A1	Q60612	Mus musculus	Predicted (SEA)	41.5715
Click to view 3D structure	Adenosine receptor A1	P47745	Cavia porcellus	Predicted (SEA)	48.5779
Click to view 3D structure	Adenosine receptor A2a	Q60613	Mus musculus	Predicted (SEA)	39.6253
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	888.571
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	2371.99
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	1478.51
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	1420.28
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	2540.61
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	1363.53
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	1084.6
Click to view 3D structure	Platelet-derived growth factor receptor alpha	P16234	Humans	Predicted (SEA)	2047.28
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	2446.96
Click to view 3D structure	Translocator protein	P30536	Humans	Predicted (SEA)	308.049
Click to view 3D structure	Adenosine receptor A2a	P46616	Cavia porcellus	Predicted (SEA)	69.3637
Click to view 3D structure	Adenosine receptor A3	P35342	Ovis aries	Predicted (SEA)	4.9045